Michelangelo’s Last Judgment in the Sistine Chapel, surely the most praised and criticized painting of the Cinquecento, emerged at the threshold of the Counter-Reformation. It offers a most original interpretation of the Last Judgment that is largely focused on the prospective terrifying fate of the damned. In this respect it recalls Buffalmacco’s Last Judgment and Inferno in the Campo Santo in Pisa whose particular emphasis on the damned and hell was without precedent in the history of medieval Last Judgments. Among the many detailed correspondences in their respective compositions some are both so unusual and close that a direct connection can be assumed to have existed. Given Pisa’s proximity to Florence Michelangelo would have known the city and its monuments.